Hydrochloric Acid → 3,5-Dinitrobenzanilide

HRID 1982196Notes

Reaction equation

HRID 1982196 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[C:14](Cl)=[O:15])([O-:10])=[O:9].Cl>O>[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[C:14]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 74323,5-Dinitrobenzoyl chloride

Product 1

HCID 3457533,5-DinitrobenzanilideYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 71 g of aniline was added 22.3 g of powdery 3,5-dinitrobenzoyl chloride with stirring. Generation of heat was observed until the temperature reached 50° C. A yellowish orange paste was obtained. The paste was stirred for 10 minutes and, then, when the liquid reaction mixture was poured into 1 l of water and the mixture was rendered acidic by concentrated hydrochloric acid (35%), a white precipitate was formed. The precipitate was recovered by filtration and dried to obtain 23.58 g of 3,5-dinitrobenzanilide (the yield was 84.6%).

Workup

  1. temperatureGeneration of heat
  2. customreached 50° C
  3. customA yellowish orange paste was obtained
  4. stirringThe paste was stirred for 10 minutes
  5. customwhen the liquid reaction mixture
  6. customa white precipitate was formed
  7. filtrationThe precipitate was recovered by filtration
  8. customdried

Sources & evidence

ORD record
ord-9f38976c9dd7491cb45db22336773f6d
Source dataset
uspto-grants-1986_06
Patent number
US04595745

Reaction notes

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